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My sister and I and 3 of my good fidners were all pregnant together. My sister and 1 friend delivered about 6 months before us, while the rest of us all delivered within 4 days of each other. It was a lot of fun to compare pregnant bellies and have someone to relate to while we were pregnant and its been even more fun to have all the babies together. In fact, my sister and I are planning our next pregnancies to happen around the same time again. So, yes, if the timing is right for everyone, I think its great to be pregnant at the same time as someone you are close to!